Tech In Boston: Podcast Uncovers Stories Behind Top Startups

It’s late Friday afternoon, and the HubSpot offices in Cambridge are closing for the day. Dave Gerhardt gathers his laptop and microphone and walks toward the T, ready to unwind after a full workweek. But instead of riding home, he heads downtown to the headquarters of HourlyNerd—a new Boston-based startup that connects businesses with freelance consultants. He walks up to the fifth floor of the downtown building and enters a conference room with Patrick Pettiti, Rob Biederman, and Peter Maglathlin, a group of recent Harvard Business School graduates. The 27-year-old Gerhardt takes five to 10 minutes to break the ice, asking questions about how the startup is performing and discussing his work as a marketing manager at HubSpot. Gerhardt then hits “record” on his device and continues the casual conversation for 30 minutes, getting a candid look at what life is like working at a new startup in Boston.

On this particular afternoon, HourlyNerd is Gerhardt’s latest project as part of his own podcast “Tech In Boston,” which offers a behind-the-scenes look at how people are building companies in the city. Gerhardt has done his homework, and his preparation for the interview stems back to the night before. On Thursday night, Gerhardt sits on his couch, doing extensive background research on his next startup, looking at LinkedIn profiles, articles, and other news written about the companies. He creates about one page of bullet points and notes to bring to the interview—just in case he needs to help guide the conversation if it starts to get a little dry. Now, sitting around a conference table with the founders of HourlyNerd, Gerhardt plunges right into his questions, provoking a laid-back conversation about some of the incredible stories behind these young companies getting started in Boston.

“I’m not trying to grill people and ask hard questions that they would get stumped on,” Gerhardt said. “It’s more like we’re hanging out over coffee or a couple beers and having a fireside chat type of scenario.”

Following the interview, Gerhardt heads home to take the next steps to disseminate his 37th podcast to date to his widespread audience. On Friday night, with the interview fresh in his mind, he spends about 30 minutes editing the audio on his laptop and filtering out any excess background noise. He saves the file and will examine it one last time for any additional tweaks before posting it the following week to his audience of over 15,000 people who subscribe to “Tech In Boston.”

“I’ve had many people tell me that this was a helpful resource for them,” Gerhardt said. “I want to motivate them to be leaders and give them the information they need to start their own companies.”

Gerhardt never wanted to be the one to create the media outlet. He had no prior experience with the podcasts, but became interested in them about a year ago when he was working downtown and commuting daily on the T. He was working for a startup named Privy at the time, and was intrigued by the stories of how companies were built and breaking into the business world. He began regularly listening to “This Week In Startups,” a podcast detailing the stories of a new startup founder or a recent millionaire who had success in San Francisco.

“I thought to myself, this would be cool if there was a Boston angle on it,” Gerhardt said.

He tweeted the idea out to a couple of friends in the tech community in Boston, asking someone to take the project forward. Many people wrote back to Gerhardt saying that he should take control of his own idea.

“I really thought I didn’t have time for this,” he said. “I wanted to have a side project—something to work on in my spare time. So I had a designer friend create a logo and I borrowed a microphone from a DJ and was ready to go.”

Immediately, “Tech In Boston” was born. Gerhardt knew that the tech community in the city was very close, and that there was always a large amount of events and people sharing information. He never expected that his small idea would be so well received.

The first interview he performed was with his boss at the time, Benjamin Jabbawy, the CEO of the young startup Privy. The two sat down in a small conference room and just had a casual conversation. Jabbawy’s startup had just 10 employees, and Gerhardt aimed to ask questions that traditional articles wouldn’t delve into, especially about creating a company out of scratch in a major city.

“We sat down and had a couple of beers and talked about the experience he had of building a company in Boston,” he said.

The podcasts came initially with a number of flaws. During Gerhardt’s first interview, the microphone was backwards and the audio was static. During others, a fire truck or ambulance would pass the conference nearly every 30 seconds during each interview and listeners couldn’t hear the details of the conversation. Some interviewees were not as charismatic or conversational as they seemed, and many did not give great face-to-face interviews, often relaying Gerhardt one-word replies. Eventually, the podcasts became more of a chore than a hobby, and Gerhard cancelled the program last May.

podcast dude
Featured Image Courtesy Of Dave Gerhardt.

“When I stopped doing them, I got a bunch of tweets and a bunch of emails from people that I didn’t know,” he said. “People that weren’t my mom—weren’t my girlfriend. That was my big moment where I thought that this could really be something great.”

Gerhardt recommitted to the podcast in early August and began performing one interview per week, sometimes via Skype if he was unable to travel. He eventually got a website up and running and started posting in a few blogs. The podcast quickly spread by word of mouth. After each episode, startup founders would introduce Gerhardt to another five emerging CEOs or prominent business leaders and investors in the area, prompting a continuous cycle of names and companies—including EverTrue, CoachUp, Common Angels, OpenView Ventures, and a Boston College alum’s startup, Drizly.

“This really was the first of its kind,” Gerhardt said.

One of the challenges of operating “This Is Boston” on a regular basis is the fact that Gerhardt works a full-time job during the week. He typically spends two to three hours after work developing the podcast each week, with additional time on the weekends. Currently, Gerhardt creates a new podcast about twice a month, depending on how he can balance his time in the office.

After leaving Privy, Gerhardt moved to his current position at the marketing and sales software company, HubSpot. HubSpot is known for its innovative “flextime policy,” allowing its employees to form their own personal work schedules. An article in the Boston Globe Magazine highlighted that the company cares about results more than how much time one spends in the office. Despite his very busy schedule, Gerhardt still finds time to pursue his hobby.

“As long as I take care of what I need to in my day job, I have the freedom to run out after lunch and meet with company downtown and come back later,” Gerhardt said. “The flexible work environment has been a big help in getting this idea off and running.”

After creating nearly 40 episodes, Gerhardt can closely monitor the progress of each individual podcast. He controls technology that allows him to track how many people on average stream each episode, and how the podcast grows over time. Currently, there is an average of 2,500 downloads per month. A dashboard also keeps track of user feedback, including content that was positively received and things that could be improved in the future.

Looking to the future, Gerhardt wants to continue spreading his love of startups and the city of Boston to as many people as possible. The podcast currently has a number of big sponsors, and Gerhardt is gaining more followers each month. He doesn’t plan on stopping anytime soon.

“Hearing the stories of 40 people who build companies in Boston is a great opportunity, and I want this podcast to be helpful resource for people to truly see what it is like to work at a startup.”

Featured Image by Francisco Ruela / Heights Graphic

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About Bennet Johnson 96 Articles
Bennet Johnson was the Metro Editor for The Heights in 2015 and Business Manager in 2016. You can probably still find him wandering around Boston, wearing his 'Minnesota Nice' T-shirt. Follow him on Twitter @bennet_15.